Omar Khadr is seen in Guantanamo Bay's Camp 4 on Oct. 23, 2010, days before the Canadian was convicted of five war crimes and sentenced to eight more years. (COLIN PERKEL/THE CANADIAN PRESS/COLIN PERKEL/THE CANADIAN PRESS)

Omar Khadr is seen in Guantanamo Bay's Camp 4 on Oct. 23, 2010, days before the Canadian was convicted of five war crimes and sentenced to eight more years.(COLIN PERKEL/THE CANADIAN PRESS/COLIN PERKEL/THE CANADIAN PRESS)

Omar Khadr, Canada’s only convicted war criminal – a confessed murderer, spy and terrorist – is headed home soon. But just how soon remains unclear. Even murkier is when he will be freed.

Mr. Khadr is eligible for repatriation any time after Monday, to serve the rest of his sentence in a Canadian prison. That could be years or as little as a few months, depending on whether he can successfully challenge the Guantanamo war crimes conviction in Canadian courts.

Mr. Khadr pleaded guilty to murder, spying and supporting terrorism as part of a plea bargain that resulted in him being sentenced to eight years, of which only the first year was to be served at Guantanamo.

After spending most of his 25 years abroad, first as a child in Pakistan as the son of a leading al-Qaeda family, followed by a brief summer learning bomb-making with Islamic jihadists in Afghanistan and nine years in Guantanamo, the Toronto-born Mr. Khadr will be eligible on Halloween to seek repatriation to Canada.

But it could take months or longer to hammer out his return, especially if Ottawa demands that he drop any further legal action as a condition of repatriation. Until then, Mr. Khadr remains one of only two convicted terrorists in a separate prison block in Guantanamo.

This week, huddled with his lawyers, Mr. Khadr may be examining his options.

He could agree to seek repatriation quietly, to serve his remaining time and try to re-enter Canadian society as unobtrusively as possible in an attempt to salvage something approaching normality for the remaining two-thirds of his life. That would require the Harper government to approve and quickly facilitate his return.

In return, lawyers familiar with his case believe Mr. Khadr would need to agree to abandon any further constitutional challenges.

But some lawyers believe Mr. Khadr could be out in less than a year if he takes his case again to the Canadian courts. They believe Mr. Khadr could challenge the U.S. war crimes conviction and the sentence, claiming both were illegal under international law. In Canada, the Supreme Court has already ruled that the government failed to properly protect Mr. Khadr’s rights.

A constitutional challenge could embarrass the government and force public disclosure of the role its agents played in Mr. Khadr’s interrogation. But it would also cast him again in the spotlight, likely making his family even more unpopular.

Many regard Mr. Khadr as a victim, an abused and gravely injured child soldier, who should never have been imprisoned by his American captors let alone put on trial for war crimes. Mr. Khadr’s trial came after U.S. President Barack Obama reversed his vow to close both the notorious offshore prison in Cuba and the Bush-era military tribunals.

Under the terms of his plea deal, Mr. Khadr’s eight-year sentence will be one-third over by July 1, 2013. At that point he would be eligible for parole under Canadian law, assuming he is, by then, in a Canadian prison. He will have spent more than 40 per cent of his life in prison: in Afghanistan’s Bagram, at Guantanamo and in whatever federal prison Ottawa opts to place him after his repatriation.

Mr. Khadr hasn’t been heard publicly since he delivered a carefully rehearsed apology at the end of his trial last October to the widow of the medic he killed in a firefight after his compound was pounded by air strikes in July of 2002, when he was 15. That apology didn’t sway the military jury that convicted him and imposed a 40-year sentence.

The U.S. military’s version of the firefight has been in dispute for years, not least because the teenager they accused of tossing the grenade that killed Special Forces Sergeant Christopher Speer suffered life-threatening head wounds and had been buried in rubble by an earlier bombing.

But in his confession, Mr. Khadr agreed to the prosecution facts.

Unknown to the jury, Mr. Khadr’s lawyers, military prosecutors and the U.S. and Canadian governments had all previously agreed to a complex plea bargain deal: a guilty plea to be followed by an eight-year sentence, one year of which was to be served in Guantanamo. That year, spent largely in solitary – away from the general detainee population because he is now serving a sentence not awaiting trial or release – ends Oct 31.

Mr. Khadr dumped the Canadian lawyers who helped craft that deal – at least the third time he has fired a legal team – and is now represented by John Norris and Brydie Bethell. Mr. Norris and Ms. Bethell are in Guantanamo this week.

Ms. Bethnell said earlier this month that a filing for Mr. Khadr’s repatriation was in process.

Mr. Khadr fired his previous Canadian lawyers; including Dennis Edney, who had offered to give him a home, summarily and without reason. Mr. Edney had long sparred with successive sets of U.S. military and civilian lawyers.

“I wholeheartedly recognize the extraordinary commitment you have shown in everything that you have done for me. … Although I feel deeply indebted to you for your dedication, changing counsel at this time is in my best interests,” Mr. Khadr said in statement then.

The Harper government, as part of Mr. Khadr’s plea deal, promised the Obama administration in writing that it was “inclined to favourably consider” any request from Mr. Khadr to transfer from the grim confinement in Guantanamo to a Canadian jail. That’s about as close as governments get to reliable promises in diplomatic-speak but significant hurdles remain – not least, who will pay the tens of thousands of dollars needed for a chartered jet to collect him from the heavily guarded U.S. military outpost in Cuba.

Mr. Khadr can’t enter the United States and Washington seems unlikely to provide a military transport to fly him to Canada. There are no commercial flights from Guantanamo, a U.S. naval base leased from Cuba. To transport anyone that the Obama administration regards as a dangerous convicted terrorist would require special security authorization as well as flight clearance.

Other Western governments, such as Britain, which demanded their citizens be returned without trial, sent military jets to get them. So did Australia as part of a plea deal that freed David Hicks. But the Harper government has so far shown no interest in getting Mr. Khadr freed or back in Canada.

Key events in Khadr’s life

Sept. 19, 1986: Omar Khadr is born in Toronto, son of, Ahmed, a notable al-Qeada figure, usually ranked 3rd of 4th after Osama bin Laden